NP-MRD: Showing NP-Card for Viniferone B (NP0027060)

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Record Information

Version

1.0

Created at

2021-06-19 18:47:24 UTC

Updated at

2021-06-29 23:52:58 UTC

NP-MRD ID

NP0027060

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Viniferone B

Provided By

JEOL Database JEOL Logo

Description

Viniferone B is found in grape seeds. It was first documented in 2004 (Fan, P., et al.). Based on a literature review very few articles have been published on Viniferone B.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192120473D          

 37 39  0  0  0  0            999 V2000
    2.4976   -0.8912    1.2135 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7890   -1.7257    0.6762 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1864   -2.3400   -0.4549 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4493   -2.2127    1.1436 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0832   -1.3530    2.2883 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9956   -2.1596    3.0562 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2107   -1.5559    3.1114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1974   -1.9884    3.6760 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1444   -0.2890    2.3910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9090   -0.1696    1.9013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3118    0.9697    1.1202 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0878    0.4779   -0.2131 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4728    1.3955   -1.0620 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1164    0.8772   -2.1846 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7134    1.7413   -3.0941 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3458    1.1882   -4.1688 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6687    3.1190   -2.9063 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0022    3.6260   -1.7904 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9404    4.9751   -1.5779 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3831    2.7781   -0.8636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3493    3.3414    0.3279 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1505    2.2640    1.0623 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3990    2.0563    0.3821 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0538   -1.9343   -0.6663 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5751   -3.2489    1.4797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2521   -2.2199    0.3015 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7169   -1.0483    2.9730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9843    0.3794    2.3122 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6595    1.2014    1.5813 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1580   -0.1960   -2.3467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6881    1.8970   -4.7378 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1427    3.7867   -3.6166 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3890    5.4371   -2.3049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0242    4.1414    0.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3969    3.7655    1.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3952    2.6201    2.0693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1886    1.6341   -0.4727 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0  0  0  0
 10  5  1  0  0  0  0
 17 18  1  0  0  0  0
 18 20  2  0  0  0  0
 15 17  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 13 14  2  0  0  0  0
 15 16  1  0  0  0  0
 14 15  1  0  0  0  0
 18 19  1  0  0  0  0
 13 12  1  0  0  0  0
 22 23  1  0  0  0  0
 20 21  1  0  0  0  0
  5  4  1  0  0  0  0
 21 22  1  0  0  0  0
  4  2  1  0  0  0  0
 22 11  1  0  0  0  0
  2  1  2  0  0  0  0
 11 12  1  0  0  0  0
  2  3  1  0  0  0  0
 13 20  1  0  0  0  0
  7  8  2  0  0  0  0
 17 32  1  0  0  0  0
 14 30  1  0  0  0  0
 21 34  1  0  0  0  0
 21 35  1  0  0  0  0
 22 36  1  1  0  0  0
 11 29  1  1  0  0  0
  5 27  1  1  0  0  0
  9 28  1  0  0  0  0
 16 31  1  0  0  0  0
 19 33  1  0  0  0  0
 23 37  1  0  0  0  0
  4 25  1  0  0  0  0
  4 26  1  0  0  0  0
  3 24  1  0  0  0  0
M  END

     RDKit          3D

 37 39  0  0  0  0  0  0  0  0999 V2000
    2.4976   -0.8912    1.2135 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7890   -1.7257    0.6762 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1864   -2.3400   -0.4549 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4493   -2.2127    1.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0832   -1.3530    2.2883 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9956   -2.1596    3.0562 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2107   -1.5559    3.1114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1974   -1.9884    3.6760 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1444   -0.2890    2.3910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9090   -0.1696    1.9013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3118    0.9697    1.1202 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0878    0.4779   -0.2131 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4728    1.3955   -1.0620 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1164    0.8772   -2.1846 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7134    1.7413   -3.0941 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3458    1.1882   -4.1688 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6687    3.1190   -2.9063 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0022    3.6260   -1.7904 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9404    4.9751   -1.5779 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3831    2.7781   -0.8636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3493    3.3414    0.3279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1505    2.2640    1.0623 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3990    2.0563    0.3821 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0538   -1.9343   -0.6663 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5751   -3.2489    1.4797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2521   -2.2199    0.3015 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7169   -1.0483    2.9730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9843    0.3794    2.3122 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6595    1.2014    1.5813 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1580   -0.1960   -2.3467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6881    1.8970   -4.7378 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1427    3.7867   -3.6166 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3890    5.4371   -2.3049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0242    4.1414    0.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3969    3.7655    1.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3952    2.6201    2.0693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1886    1.6341   -0.4727 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0
 10  5  1  0
 17 18  1  0
 18 20  2  0
 15 17  2  0
  5  6  1  0
  6  7  1  0
  7  9  1  0
  9 10  2  0
 13 14  2  0
 15 16  1  0
 14 15  1  0
 18 19  1  0
 13 12  1  0
 22 23  1  0
 20 21  1  0
  5  4  1  0
 21 22  1  0
  4  2  1  0
 22 11  1  0
  2  1  2  0
 11 12  1  0
  2  3  1  0
 13 20  1  0
  7  8  2  0
 17 32  1  0
 14 30  1  0
 21 34  1  0
 21 35  1  0
 22 36  1  1
 11 29  1  1
  5 27  1  1
  9 28  1  0
 16 31  1  0
 19 33  1  0
 23 37  1  0
  4 25  1  0
  4 26  1  0
  3 24  1  0
M  END


  Mrv1652306192120473D          

 37 39  0  0  0  0            999 V2000
    2.4976   -0.8912    1.2135 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7890   -1.7257    0.6762 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1864   -2.3400   -0.4549 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4493   -2.2127    1.1436 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0832   -1.3530    2.2883 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9956   -2.1596    3.0562 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2107   -1.5559    3.1114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1974   -1.9884    3.6760 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1444   -0.2890    2.3910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9090   -0.1696    1.9013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3118    0.9697    1.1202 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0878    0.4779   -0.2131 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4728    1.3955   -1.0620 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1164    0.8772   -2.1846 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7134    1.7413   -3.0941 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3458    1.1882   -4.1688 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6687    3.1190   -2.9063 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0022    3.6260   -1.7904 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9404    4.9751   -1.5779 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3831    2.7781   -0.8636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3493    3.3414    0.3279 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1505    2.2640    1.0623 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3990    2.0563    0.3821 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0538   -1.9343   -0.6663 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5751   -3.2489    1.4797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2521   -2.2199    0.3015 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7169   -1.0483    2.9730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9843    0.3794    2.3122 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6595    1.2014    1.5813 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1580   -0.1960   -2.3467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6881    1.8970   -4.7378 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1427    3.7867   -3.6166 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3890    5.4371   -2.3049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0242    4.1414    0.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3969    3.7655    1.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3952    2.6201    2.0693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1886    1.6341   -0.4727 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0  0  0  0
 10  5  1  0  0  0  0
 17 18  1  0  0  0  0
 18 20  2  0  0  0  0
 15 17  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 13 14  2  0  0  0  0
 15 16  1  0  0  0  0
 14 15  1  0  0  0  0
 18 19  1  0  0  0  0
 13 12  1  0  0  0  0
 22 23  1  0  0  0  0
 20 21  1  0  0  0  0
  5  4  1  0  0  0  0
 21 22  1  0  0  0  0
  4  2  1  0  0  0  0
 22 11  1  0  0  0  0
  2  1  2  0  0  0  0
 11 12  1  0  0  0  0
  2  3  1  0  0  0  0
 13 20  1  0  0  0  0
  7  8  2  0  0  0  0
 17 32  1  0  0  0  0
 14 30  1  0  0  0  0
 21 34  1  0  0  0  0
 21 35  1  0  0  0  0
 22 36  1  1  0  0  0
 11 29  1  1  0  0  0
  5 27  1  1  0  0  0
  9 28  1  0  0  0  0
 16 31  1  0  0  0  0
 19 33  1  0  0  0  0
 23 37  1  0  0  0  0
  4 25  1  0  0  0  0
  4 26  1  0  0  0  0
  3 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0027060

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C([H])([H])[C@]1([H])OC(=O)C([H])=C1[C@@]1([H])OC2=C([H])C(O[H])=C([H])C(O[H])=C2C([H])([H])[C@@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O8/c16-6-1-9(17)7-3-10(18)15(23-11(7)2-6)8-4-14(21)22-12(8)5-13(19)20/h1-2,4,10,12,15-18H,3,5H2,(H,19,20)/t10-,12+,15-/m1/s1

> <INCHI_KEY>
KUJDOUXXVFFHCT-IFUGULHKSA-N

> <FORMULA>
C15H14O8

> <MOLECULAR_WEIGHT>
322.269

> <EXACT_MASS>
322.068867411

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
29.91275726348192

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(2S)-5-oxo-3-[(2R,3R)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-2-yl]-2,5-dihydrofuran-2-yl]acetic acid

> <ALOGPS_LOGP>
0.97

> <JCHEM_LOGP>
0.4703104283333333

> <ALOGPS_LOGS>
-2.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.6499035883529847

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.3624636238278147

> <JCHEM_PKA_STRONGEST_BASIC>
-3.276219061661828

> <JCHEM_POLAR_SURFACE_AREA>
133.52

> <JCHEM_REFRACTIVITY>
74.92229999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.06e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2S)-5-oxo-3-[(2R,3R)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-2-yl]-2H-furan-2-yl]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 37 39  0  0  0  0  0  0  0  0999 V2000
    2.4976   -0.8912    1.2135 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7890   -1.7257    0.6762 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1864   -2.3400   -0.4549 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4493   -2.2127    1.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0832   -1.3530    2.2883 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9956   -2.1596    3.0562 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2107   -1.5559    3.1114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1974   -1.9884    3.6760 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1444   -0.2890    2.3910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9090   -0.1696    1.9013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3118    0.9697    1.1202 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0878    0.4779   -0.2131 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4728    1.3955   -1.0620 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1164    0.8772   -2.1846 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7134    1.7413   -3.0941 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3458    1.1882   -4.1688 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6687    3.1190   -2.9063 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0022    3.6260   -1.7904 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9404    4.9751   -1.5779 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3831    2.7781   -0.8636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3493    3.3414    0.3279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1505    2.2640    1.0623 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3990    2.0563    0.3821 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0538   -1.9343   -0.6663 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5751   -3.2489    1.4797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2521   -2.2199    0.3015 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7169   -1.0483    2.9730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9843    0.3794    2.3122 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6595    1.2014    1.5813 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1580   -0.1960   -2.3467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6881    1.8970   -4.7378 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1427    3.7867   -3.6166 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3890    5.4371   -2.3049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0242    4.1414    0.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3969    3.7655    1.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3952    2.6201    2.0693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1886    1.6341   -0.4727 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0
 10  5  1  0
 17 18  1  0
 18 20  2  0
 15 17  2  0
  5  6  1  0
  6  7  1  0
  7  9  1  0
  9 10  2  0
 13 14  2  0
 15 16  1  0
 14 15  1  0
 18 19  1  0
 13 12  1  0
 22 23  1  0
 20 21  1  0
  5  4  1  0
 21 22  1  0
  4  2  1  0
 22 11  1  0
  2  1  2  0
 11 12  1  0
  2  3  1  0
 13 20  1  0
  7  8  2  0
 17 32  1  0
 14 30  1  0
 21 34  1  0
 21 35  1  0
 22 36  1  1
 11 29  1  1
  5 27  1  1
  9 28  1  0
 16 31  1  0
 19 33  1  0
 23 37  1  0
  4 25  1  0
  4 26  1  0
  3 24  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  O   UNK     0       2.498  -0.891   1.214  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.789  -1.726   0.676  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.186  -2.340  -0.455  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.449  -2.213   1.144  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.083  -1.353   2.288  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.996  -2.160   3.056  0.00  0.00           O+0
HETATM    7  C   UNK     0      -2.211  -1.556   3.111  0.00  0.00           C+0
HETATM    8  O   UNK     0      -3.197  -1.988   3.676  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.144  -0.289   2.391  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.909  -0.170   1.901  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.312   0.970   1.120  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.088   0.478  -0.213  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.473   1.395  -1.062  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.116   0.877  -2.185  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.713   1.741  -3.094  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.346   1.188  -4.169  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.669   3.119  -2.906  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.002   3.626  -1.790  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.940   4.975  -1.578  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.383   2.778  -0.864  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.349   3.341   0.328  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.151   2.264   1.062  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.399   2.056   0.382  0.00  0.00           O+0
HETATM   24  H   UNK     0       3.054  -1.934  -0.666  0.00  0.00           H+0
HETATM   25  H   UNK     0       0.575  -3.249   1.480  0.00  0.00           H+0
HETATM   26  H   UNK     0      -0.252  -2.220   0.302  0.00  0.00           H+0
HETATM   27  H   UNK     0       0.717  -1.048   2.973  0.00  0.00           H+0
HETATM   28  H   UNK     0      -2.984   0.379   2.312  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.660   1.201   1.581  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.158  -0.196  -2.347  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.688   1.897  -4.738  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.143   3.787  -3.617  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.389   5.437  -2.305  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.024   4.141   0.002  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.397   3.765   1.011  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.395   2.620   2.069  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.189   1.634  -0.473  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    4    1    3                                                  
CONECT    3    2   24                                                       
CONECT    4    5    2   25   26                                             
CONECT    5   10    6    4   27                                             
CONECT    6    5    7                                                       
CONECT    7    6    9    8                                                  
CONECT    8    7                                                            
CONECT    9    7   10   28                                                  
CONECT   10   11    5    9                                                  
CONECT   11   10   22   12   29                                             
CONECT   12   13   11                                                       
CONECT   13   14   12   20                                                  
CONECT   14   13   15   30                                                  
CONECT   15   17   16   14                                                  
CONECT   16   15   31                                                       
CONECT   17   18   15   32                                                  
CONECT   18   17   20   19                                                  
CONECT   19   18   33                                                       
CONECT   20   18   21   13                                                  
CONECT   21   20   22   34   35                                             
CONECT   22   23   21   11   36                                             
CONECT   23   22   37                                                       
CONECT   24    3                                                            
CONECT   25    4                                                            
CONECT   26    4                                                            
CONECT   27    5                                                            
CONECT   28    9                                                            
CONECT   29   11                                                            
CONECT   30   14                                                            
CONECT   31   16                                                            
CONECT   32   17                                                            
CONECT   33   19                                                            
CONECT   34   21                                                            
CONECT   35   21                                                            
CONECT   36   22                                                            
CONECT   37   23                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   78    0
END

RDKit          3D

37 39  0  0  0  0  0  0  0  0999 V2000
    2.4976   -0.8912    1.2135 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7890   -1.7257    0.6762 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1864   -2.3400   -0.4549 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4493   -2.2127    1.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0832   -1.3530    2.2883 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9956   -2.1596    3.0562 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2107   -1.5559    3.1114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1974   -1.9884    3.6760 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1444   -0.2890    2.3910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9090   -0.1696    1.9013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3118    0.9697    1.1202 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0878    0.4779   -0.2131 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4728    1.3955   -1.0620 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1164    0.8772   -2.1846 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7134    1.7413   -3.0941 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3458    1.1882   -4.1688 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6687    3.1190   -2.9063 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0022    3.6260   -1.7904 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9404    4.9751   -1.5779 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3831    2.7781   -0.8636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3493    3.3414    0.3279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1505    2.2640    1.0623 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3990    2.0563    0.3821 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0538   -1.9343   -0.6663 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5751   -3.2489    1.4797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2521   -2.2199    0.3015 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7169   -1.0483    2.9730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9843    0.3794    2.3122 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6595    1.2014    1.5813 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1580   -0.1960   -2.3467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6881    1.8970   -4.7378 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1427    3.7867   -3.6166 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3890    5.4371   -2.3049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0242    4.1414    0.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3969    3.7655    1.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3952    2.6201    2.0693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1886    1.6341   -0.4727 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0
 10  5  1  0
 17 18  1  0
 18 20  2  0
 15 17  2  0
  5  6  1  0
  6  7  1  0
  7  9  1  0
  9 10  2  0
 13 14  2  0
 15 16  1  0
 14 15  1  0
 18 19  1  0
 13 12  1  0
 22 23  1  0
 20 21  1  0
  5  4  1  0
 21 22  1  0
  4  2  1  0
 22 11  1  0
  2  1  2  0
 11 12  1  0
  2  3  1  0
 13 20  1  0
  7  8  2  0
 17 32  1  0
 14 30  1  0
 21 34  1  0
 21 35  1  0
 22 36  1  1
 11 29  1  1
  5 27  1  1
  9 28  1  0
 16 31  1  0
 19 33  1  0
 23 37  1  0
  4 25  1  0
  4 26  1  0
  3 24  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₄O₈

Average Mass

322.2690 Da

Monoisotopic Mass

322.06887 Da

IUPAC Name

2-[(2S)-5-oxo-3-[(2R,3R)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-2-yl]-2,5-dihydrofuran-2-yl]acetic acid

Traditional Name

[(2S)-5-oxo-3-[(2R,3R)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-2-yl]-2H-furan-2-yl]acetic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C([H])([H])[C@]1([H])OC(=O)C([H])=C1[C@@]1([H])OC2=C([H])C(O[H])=C([H])C(O[H])=C2C([H])([H])[C@@]1([H])O[H]

InChI Identifier

InChI=1S/C15H14O8/c16-6-1-9(17)7-3-10(18)15(23-11(7)2-6)8-4-14(21)22-12(8)5-13(19)20/h1-2,4,10,12,15-18H,3,5H2,(H,19,20)/t10-,12+,15-/m1/s1

InChI Key

KUJDOUXXVFFHCT-IFUGULHKSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Vitis vinifera L.	JEOL database	Fan, P., et al, Tetrahedron Letts. 45, 3163 (2004)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

1-benzopyrans

Alternative Parents

Substituents

1-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
2-furanone
Dicarboxylic acid or derivatives
Benzenoid
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Dihydrofuran
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Polyol
Carboxylic acid derivative
Ether
Carboxylic acid
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Carbonyl group
Alcohol
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.97	ALOGPS
logP	0.47	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	2.36	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.52 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	74.92 m³·mol⁻¹	ChemAxon
Polarizability	29.91 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101345908

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Fan, P., et al. (2004). Fan, P., et al, Tetrahedron Letts. 45, 3163 (2004). Tetrahedron Lett.

Showing NP-Card for Viniferone B (NP0027060)

MOL for NP0027060 (Viniferone B)

3D MOL for NP0027060 (Viniferone B)

3D SDF for NP0027060 (Viniferone B)

3D-SDF for NP0027060 (Viniferone B)

PDB for NP0027060 (Viniferone B)

3D PDB for NP0027060 (Viniferone B)

SMILES for NP0027060 (Viniferone B)

INCHI for NP0027060 (Viniferone B)

Structure for NP0027060 (Viniferone B)

3D Structure for NP0027060 (Viniferone B)